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The Green Hills of Cunningham

If courage is grace under fire, as Hemingway once wrote, then Sandy Cunningham is as courageous as they come. From a childhood in war-torn Rhodesia to living in a tent in Kenyan lion country, the owner of a bespoke travel company sees the future of adventure travel in the globe’s uncharted corners, where travelers take control of their own narratives.


One night not too long ago, Sandy Cunningham was home alone, asleep, when her dog started growling. Probably nothing, she thought, but in the dim light she could see that the dog’s hackles were on end. Then a motion-detector light flicked on outside. Cunningham bolted out of bed and grabbed the machete off the floor.

Cunningham and her husband, Chip, live on the outskirts of Santa Fe, New Mexico, surrounded by the dusty hills and scrublands that remind them of their years in Africa. There really aren’t too many places for an intruder to hide in that kind of sun-beaten country, but it was dark, and something clearly wasn’t right. She padded out toward a window for a closer look.

Cunningham has never been one to shy away from danger. Growing up in Rhodesia (now Zimbabwe) during the 15-year Bush War for independence in the sixties and seventies, Cunningham knew what it was like to be afraid. But she also knew how to put fear in its place, to let her curiosity flourish and journey into the unknown.

That sentiment now lies at the crux of what makes Cunningham one of the most creative adventure travel experts working with off-the-beaten track destinations around the globe today. As a co-owner of Uncharted Outposts—now known as Outside Go—Cunningham and her husband specialize in sending people to the places they’ve always longed to see, in ways that are right for them. Want to climb Everest? Sure. Visit safari camps by plane or learn how to surf in Nicaragua? No problem. Cunningham can rely on her own vast library of adventures to build the right custom trip.

“The world is just such a huge oyster right now in terms of what people can do and what they can achieve,” she says. “We match people’s dreams to the experiences.”

Over the course of her decades-long career, Cunningham has seen adventure travel grow from a fringe product into a multi-billion-dollar industry now popular enough to risk being “cookie cutter,” she says. Companies now offer thick catalogs with nearly identical trips to Nepal, the Galápagos (with a Machu Picchu extension), and Australia. “People are really looking for uncharted waters in the travel industry now,” she observes. “They don’t want to ‘join’ a trip. They want a vested interest in crafting it. They want to be part of the design and the creative process.”

Cunningham was pretty invested in her own experiences from a very young age. As communists, nationalists, and thugs battled for power in British-ruled Rhodesia, Cunningham remembers ducking in the back of her family’s station wagon as gunfire peppered its side. Her father believed in the country’s future, which was torn in an epic battle between communism and freedom. Cunningham admired the ways he navigated around the uncertainties of war. “The decision was quite simple, really,” Cunningham says. “We could stay put and never go anywhere, or we could have a life. We weren’t going to live in fear, and so we traveled. That’s what took me to the next level in life.”

So instead of staying put, the family would travel out of Salisbury (now Harare) in armored convoys and go on safari anyway. They’d get rooms at the elegant Victoria Falls Hotel, but on the far side of the building, which was out of range of the rebel-fired mortar rockets.

As a teenager, Cunningham followed her family out of Rhodesia to South Africa and then England to finish high school. In 1987 she took a gap year to study hospitality in Gstaad, Switzerland, where she met Chip, her husband to be. The two eventually bought tickets to the United States, loaded mountain bikes into a forest-green Isuzu Trooper, and spent three months road-tripping, mostly around the American West, on about $10 a day.

“All Africans grow up with a desire to see the American West,” she explains. “That frontier spirit seems so embodied there. Every single day was amazing.”

The couple settled briefly in Santa Fe before Chip got a work permit to be a bush pilot in Kenya. Sandy eventually found work there managing a group of restaurants and properties in Nairobi, but the city wasn’t where they wanted to be. Then one day Richard Bonham, a pioneer in the East Africa safari business and an ardent conservationist, called. His lodge, Ol Donyo Wuas, deep in Hemingway’s Green Hills of Africa and one of the continent’s finest, had burned down, and he needed an experienced bush pilot and an expert manager to help rebuild it. Would they be interested?

“This was something we could define, build, make our own and have an imprint on the world,” Cunningham says. “To come into a place and replace the managers is fun, but it’s not a challenge. Chip loved the idea of flying in and out of there, buzzing zebras off the runway. This was the Africa of Hemingway. We said yes.”

The two lived in a tent on the property, among some of the mangiest, fiercest lions in Africa, as workers rebuilt the lodge. Their three-legged rottweiler got taken out by a hartebeest. They were chased by ostriches and had to hide in trees. One time a lion attacked a young teenager from a nearby community, puncturing his lungs and turning his back into a sucking wound.

“There were very real and scary dangers living there,” Cunningham says. “And yet it was magical. Terrifying and still paradise.”

Movie stars, Supreme Court justices, and ordinary people who’d saved up everything to make a dream come true arrived on their grass strip once the work was complete. Cunningham had talked to each of them in depth before arriving, helping to make the experience just right for them. They’d ride horses and look for rhinos or take guests to secluded spots for cocktails and a sunset. They’d wake up looking at Kilimanjaro, a purple giant on the horizon, and take parents and kids out to see their first giraffe.

“Africa brings out so much in people,” she says. So many years later, bringing that joy to people still shapes her work. Even now, back in the United States, Africa is with them every day— in the landscape, the sunsets, the way they deal with danger.

It was with her that night she walked to the window wielding a machete. She peered outside just in time to see the perpetrator lumbering along a walkway: a bear. A wave of relief washed over her.

“I don’t feel the need ever to run away,” she says. “That is what my father taught us—to believe in something and see it through.”

Sandy Cunningham has endured many hardships and obstacles while establishing herself as a leader in the adventure travel industry. Sandy developed the kind of character that believes fear is not what stands in our way, but how we overcome that fear is what defines us as individuals. TUDOR Watch is proudly celebrating the legacy and heritage of adventure travel. The sort of adventure that excites our imaginations and transforms our bodies into vessels of discovery. The spirit of adventure travel lives on through the TUDOR Heritage Ranger, which honors the fortitude of those who have fearlessly pushed beyond their own limits to pave the way for future generations to come.

Check out the Heritage Ranger Here.